EP2252144B1 - Verwendung von esteramiden als lösungsmittel, esteramide als solche, sowie verfahren zur herstellung von esteramiden - Google Patents

Verwendung von esteramiden als lösungsmittel, esteramide als solche, sowie verfahren zur herstellung von esteramiden Download PDF

Info

Publication number
EP2252144B1
EP2252144B1 EP09704290.7A EP09704290A EP2252144B1 EP 2252144 B1 EP2252144 B1 EP 2252144B1 EP 09704290 A EP09704290 A EP 09704290A EP 2252144 B1 EP2252144 B1 EP 2252144B1
Authority
EP
European Patent Office
Prior art keywords
crystal clear
limpide
conet
conme
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
EP09704290.7A
Other languages
English (en)
French (fr)
Other versions
EP2252144A1 (de
Inventor
Olivier Jentzer
Massimo Guglieri
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Specialty Operations France SAS
Original Assignee
Rhodia Operations SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from FR0800393A external-priority patent/FR2926699B1/fr
Application filed by Rhodia Operations SAS filed Critical Rhodia Operations SAS
Priority to EP18198337.0A priority Critical patent/EP3520613A1/de
Priority to EP10190722A priority patent/EP2347652A1/de
Publication of EP2252144A1 publication Critical patent/EP2252144A1/de
Application granted granted Critical
Publication of EP2252144B1 publication Critical patent/EP2252144B1/de
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/20—Diluents or solvents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D9/00—Chemical paint or ink removers
    • C09D9/005—Chemical paint or ink removers containing organic solvents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/32—Amides; Substituted amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/43—Solvents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3263—Amides or imides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • C11D7/5013—Organic solvents containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides

Definitions

  • the subject of the present invention is the use as solvents of compounds of the esteramide type. It also relates to particularly convenient processes for the preparation of esteramides. It also relates to new esteramides, which can in particular be used as solvents, for example in phytosanitary formulations.
  • solvents for example to prepare chemicals and materials, to formulate chemical compounds, or to treat surfaces.
  • solvents are used for the formulation of phytosanitary active ingredients, in particular in the form of emulsifiable concentrates (Emulsifiable Concentrate “EC”) intended to be diluted in water by the farmer, before application to a field.
  • EC emulsifiable Concentrate
  • dialkylamides as solvents. These are products of formula R—CONMe 2 where R is a hydrocarbon group such as an alkyl, typically C 6 -C 30 . Such products are in particular marketed under the name Genagen® by the company Clariant. These solvents find applications in particular in the phytosanitary field.
  • Diesters of dicarboxylic acids are also known as solvents, in particular the diesters obtained by esterification of a mixture of adipic acid, glutaric acid and succinic acid. Such products are in particular marketed under the names Rhodiasolv® RPDE and Rhodiasolv® DIB by the company Rhodia.
  • the compound of formula L: MeOOC-CHEt-CH 2 -CONMe 2 was identified by the CAS Registry Number® 368212-04-8 , with reference to the document WO 01/79167 relating to a distant domain, and the relevance of which is doubtful.
  • the compound of formula M MeOOC-CH 2 -CH(CH 3 )-CH 2 -CONH(n-butyl) was identified by the CAS Registry Number® 538326-02-2 , with reference to a document relating to enzymatic reactions.
  • the compound of formula N MeOOC-CH 2 -CH(CH 3 )-CH 2 -CONMe 2 was identified by the CAS Registry Number® 70367-41-8 , with reference to a document relating to the use of lithium enolates.
  • Example 9 The document US 3,417,114 described in Example 9 the compound designated by DMGME, of formula O:MeOOC-CH 2 -CH 2 -CH 2 -CONMe 2 .
  • This compound is prepared by reacting dimethyl glutarate with dimethylamine, then isolating the DMGME by distillation from the resulting complex mixture (it is actually a by-product).
  • DMGME is said to have a melting point of 7.5°C.
  • the compound of formula P: MeOOC-CH 2 -CH 2 -CONMe 2 was identified by the CAS Registry Number® 30891-34-0 , in reference to documents relating to distant domains, and whose relevance is doubtful.
  • the document DE 1040234 describes the following compounds and their use as plasticizers: C4H9 - OOC- CH2 - CH2 - CONEt2 C 6 H 13 -OOC-(CH 2 ) 8 -CON(C 3 H 7 ) 2 C 8 H 17 -OOC-(CH 2 ) 8 -CON(C 4 H 9 ) 2 C 8 H 17 -OOC-(CH 2 ) 8 -CON(C 8 H 17 ) 2
  • solvent is understood in a broad sense, covering in particular the functions of co-solvent, of crystallization inhibitor.
  • the term solvent can in particular designate a liquid product at the temperature of use, preferably with a melting point less than or equal to 20°C, preferably at 5°C, preferably at 0°C, which can contribute to making liquid a solid matter, or to prevent or retard the solidification or crystallization of matter in a liquid medium.
  • composition of matter is meant a composition, more or less complex, comprising several chemical compounds. It may typically be an unpurified or modestly purified reaction product.
  • the compound of the invention may in particular be isolated and/or marketed and/or used in the form of a composition of matter comprising it. If the compound of the invention is a mixture of several compounds among those listed according to the present claim 1 then it is also a composition of matter.
  • the compound of the invention in the form of a pure molecule or in the form of a mixture among those listed according to the present claim 1, can be included in a composition of matter.
  • the compound of the invention may represent at least 10% by weight.
  • it is the main compound of the composition of matter.
  • main compound is meant in the present application, the compound whose content is the highest, even if its content is less than 50% by weight (for example in a mixture of 40% of A, 30% of B, and 30% C, product A is the main compound).
  • the compound of the invention represents at least 50% by weight of the composition of matter, for example from 70 to 95% by weight, and even from 75 to 90% by weight.
  • the composition of matter can be a reaction product.
  • the compound of the invention should be construed as the compound which is used in the present invention and is selected from the list above.
  • the esteramide has a melting point lower than or equal to 20°C, preferably 5°C, preferably 0°C.
  • the compound of the invention can be prepared by any appropriate method. It is possible in particular to implement a reaction step of an anhydride of formula (I′), with an alcohol of formula R 1 —OH and/or an amine of formula HNR 2 R 3
  • the anhydride can be prepared during a step a) prior to cyclization of a diacid of formula HOOC-A-COOH, preferably by reaction of the diacid with acetic anhydride.
  • One can in particular carry out a reflux in an excess of acetic anhydride.
  • a condensation of the product of formula (I′) can be carried out.
  • Step 1b) is preferably carried out using at least 1 molar equivalent of alcohol, relative to the anhydride. It is possible to use a large excess of alcohol, for example from 2 to 20 equivalents, in particular from 5 to 15. It is possible in particular to use alcohol as solvent for the reaction.
  • step 1c) comprises the following steps (which can be simultaneous or subsequent, preferably subsequent): 1c1) the compound of formula (I") is converted into an acyl chloride of formula (I′′′) below, preferably by reaction with thionyl chloride, R1 -OOC-A-COCl(I′′′) 1c2) the compound of formula (I′′′) is reacted with the amine of formula HNR 3 R 4 so as to obtain the compound of formula (I).
  • Stage 1c2) is accompanied by the formation of hydrochloric acid. It is possible to use a base in order to trap it, for example triethanolamine or triethylamine (TEA). This step can be implemented with at least 0.8 molar equivalent of amine, preferably with at least one equivalent. It is possible in particular to use an excess of 1.05 to 1.4 molar equivalents.
  • a base for example triethanolamine or triethylamine (TEA).
  • TAA triethylamine
  • step 3b is generally unnecessary. Otherwise, this step will typically be implemented.
  • the starting point is the diester having the desired R 1 group.
  • step 3a) preferably 0.7 to 1.5, for example 0.8 to 1.2 mol, preferably 0.9 to 1.1 mol, preferably about 1 mol , of amine per mole of diester. It is advantageous to operate with a slight excess, such as an excess of at least 1.05 mole of amine per mole of diester, for example from 1.05 to 1.1 mole of amine per mole of diester.
  • Stage 3a) can be carried out in solution, for example in aqueous solution, or in solution in a solvent such as toluene or an alcohol. It is preferred to operate in a non-aqueous solution, avoiding any presence of water. It is possible during this step to gradually eliminate the methanol formed in order to promote the reaction. The elimination can be accompanied by an elimination of the solvent, for example at an azeotrope. After separation of the methanol, the removed solvent can be reintroduced into the process. Stage 3a) is preferably carried out in the presence of a catalyst, in particular a catalyst of the basic type. It is for example possible to use methoxides such as MeONa, carbonates such as K 2 CO 3 , Na 2 CO 3 , titanates.
  • a catalyst in particular a catalyst of the basic type. It is for example possible to use methoxides such as MeONa, carbonates such as K 2 CO 3 , Na 2 CO 3 , titanates.
  • Step 3b) is a trans-esterification step. It can in particular be catalyzed by acids or bases, for example by K 2 CO 3 , or Na 2 CO 3
  • the reaction can be followed by filtration and/or purification steps, for example by distillation.
  • the diacids can in particular be obtained from a mixture of dinitrile compounds, where appropriate in the form of mixtures.
  • the dinitriles can in particular be dinitriles produced and recovered in the process for the manufacture of adiponitrile by double hydrocyanation of butadiene. In this case, it may be mixtures of dinitriles. This process used on a large scale in industry to produce the vast majority of adiponitrile consumed in the world is described in numerous patents and works.
  • the hydrocyanation reaction of butadiene mainly leads to the formation of linear dinitriles but also to the formation of branched dinitriles, the two main ones of which are methylglutaronitrile and ethylsuccinonitrile.
  • the branched dinitrile compounds are separated by distillation and recovered, for example, as an overhead fraction in a distillation column.
  • Useful diacids can be obtained by reaction between the dinitrile compounds and an inorganic base, to obtain acid salts, then neutralization of these salts with an acid. Useful diacids can also be obtained by acid hydrolysis of dinitrile compounds.
  • Diesters of formula R 1 OOC-A-COOR 1 which are useful for implementing sequence 3 are commercially available, in particular from Invista under the references DBE, or from Rhodia under the name Rhodiasolv® RPDE.
  • the compound of the invention and/or a composition of matter comprising it described above can in particular be used in phytosanitary formulations comprising a solid active product. More details are given below, where the word "solvent" can designate the compound of the invention or a composition of matter comprising it, described above.
  • the phytosanitary formulation is generally a concentrated phytosanitary formulation comprising an active compound.
  • the phytosanitary formulations must allow easy dilution by weight by the farmer, in order to obtain a product in which the phytosanitary product is correctly dispersed, for example in the form of a solution, emulsion, suspension, or suspension. emulsion.
  • Phytosanitary formulations thus allow the transport of a phytosanitary product in relatively concentrated form, easy packaging and/or easy handling for the end user.
  • Different types of phytosanitary formulations can be used according to the different phytosanitary products.
  • Emulsifiable Concentrates Emulsifiable Concentrates
  • EW concentrated emulsions
  • ME microemulsions
  • WP wettable powders
  • WDG water dispersible granules
  • the phytosanitary product After dilution by weight by the farmer, for example by mixing with water, the phytosanitary product can be found in different physical forms: solution, dispersion of solid particles, dispersion of droplets of the product, droplets of solvent in which the product is dissolved.
  • Phytosanitary formulations generally include compounds that make it possible to obtain these physical forms. They may, for example, be surfactants, solvents, mineral carriers and/or dispersants. Very often these compounds do not have an active character, but a character of an intermediate aid to the formulation.
  • the phytosanitary formulations can in particular be in liquid form, or in solid form.
  • the phytosanitary formulation thus comprises a solution of the product in the solvent.
  • the formulation can be in solid form, for example in the form of a wettable powder (WP) where the solution impregnates an inorganic carrier, for example kaolin and/or silica.
  • WP wettable powder
  • the formulation can alternatively be in liquid form, for example in the form of an emulsifiable concentrate (EC) having a single clear liquid phase comprising the solvent and the product in solution, which can form an emulsion by adding water, without stirring or with a low hustle.
  • EC emulsifiable concentrate
  • EW cloudy concentrated emulsion
  • ME clear microemulsion
  • Some solid phytosanitary actives are often difficult to formulate.
  • tebuconazole is a particularly effective fungicide, and widely used, in particular for the cultivation of soybeans.
  • Active phytosanitary products in particular non-water-soluble and solid products, are known to those skilled in the art.
  • the active phytosanitary product can in particular be a herbicide, an insecticide, an acaricide, a fungicide, or an agent for eliminating rodents ("rodenticide" in English), for example a rat poison.
  • suitable active materials mention may be made, inter alia, of Ametryne, Diuron, Linuron, Chlortoluron, Isoproturon, Nicosulfuron, Metamitron, Diazinon, Aclonifen, Atrazine , Chlorothalonil, Bromoxynil, Bromoxynil heptanoate, Bromoxynil octanoate, Mancozeb, Maneb, Zineb, Phenmedipham, Propanyl, phenoxyphenoxy series, heteroaryloxyphenoxy series, CMPP, MCPA, 2,4 -D, Simazine, the active products of the imidazolinone series, the organophosphate family, with in particular Azinphos-ethyl, Azinphos-methyl, Alachlor, Chlorpyriphos, Diclofop-methyl, Fenoxaprop-p -ethyl, Methoxychlor, Cypermethrin, Fenoxycar
  • the water-insoluble products are chosen from this list.
  • the following active phytosanitary products can be used: Alachlor Chlorpyrifos alpha-cypermethrin As a racemic mixture and/or as isolated stereoisomers. Phenmedipham propanil Pendimethalin triadimenol Trifluralin Oxyfluorfen Dimethoate Imidacloprid Proxopur Benomyl Deltamethrin Fenvalerate Abamectin Amicarbazone Bifenthrin Carbosulfan Cyfluthrin Difenconazole Ethofenprox Fenoxaprop-ethyl Fipronil Fenvalerate Fluazifop-p-butyl Flufenouron Hexazinone Lambda-cyalothrin Methomyl Permethrin Prochloraz Propiconazole Tebuconazole
  • the phytosanitary formulation can comprise an emulsifying agent, typically and preferably a surfactant.
  • Emulsifying agents are agents intended to facilitate emulsification or dispersion after bringing the formulation into contact with water, and/or to stabilize (over time and/or temperature) the emulsion or dispersion , for example by avoiding sedimentation.
  • Surfactants are known compounds, which generally have a relatively low molar mass, for example less than 1000 g/mol.
  • the surfactant can be an anionic surfactant in salified or acid form, nonionic, preferably polyalkoxylated, cationic, amphoteric (term also including zwitterionic surfactants). It may be a mixture or a combination of these surfactants.
  • the anionic surfactants can be in acid form (they are potentially anionic), or in a partially or totally salified form, with a counterion.
  • the counter-ion can be an alkali metal, such as sodium or potassium, an alkaline-earth metal, such as calcium, or even an ammonium ion of formula N(R) 4 + in which R, which are identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical optionally substituted by an oxygen atom.
  • the formulation advantageously comprises at least 4%, preferably at least 5%, preferably at least 8%, by weight of dry matter, of at least one surfactant c).
  • the solvent can be combined with an aromatic and/or non-aromatic surfactant.
  • the concentrated phytosanitary formulation preferably does not include large amounts of water.
  • the water content is less than 50% by weight, advantageously less than 25% by weight. It will generally be less than 10% by weight.
  • the formulation is preferably a liquid formulation, for example in the form of an emulsifiable concentrate (EC), a concentrated emulsion (EW) or a microemulsion (ME).
  • EC emulsifiable concentrate
  • EW concentrated emulsion
  • ME microemulsion
  • it preferably comprises less than 500 g/L of water, more preferably less than 250 g/L. It will generally be less than 100 g/L.
  • solid formulations for example formulations in which a liquid comprising the phytosanitary product dissolved in the solvent, is supported by a mineral and/or dispersed in a solid matrix.
  • the formulation can of course include other ingredients (or "other additives") than the active phytosanitary product, the solvent(s), the emulsifying agent(s) optional(s) and optional water. It may in particular comprise agents for modifying the viscosity, antifoam agents, in particular silicone antifoams, anti-rebound agents, anti-leaching agents, inert fillers, in particular mineral fillers, anti-freeze agents, etc.
  • the concentrated phytosanitary formulation is intended to be spread over a cultivated field or to be cultivated, for example a soybean field, most often after dilution in water, to obtain a diluted composition.
  • the dilution is generally carried out by the farmer, directly in a reservoir ("tank-mix"), for example in the reservoir of a device intended to spread the composition.
  • the operator adds other phytosanitary products, for example fungicides, herbicides, pesticides, insecticides, fertilizers.
  • the formulation can be used to prepare a composition diluted in water of the active phytosanitary product, by mixing at least one part by weight of concentrated formulation with at least 10 parts of water, preferably less than 1000 parts.
  • the dilution rates and quantities to be applied to the field generally depend on the phytosanitary product and the desirable dose to treat the field; this can be determined by the farm operator. Other details or advantages may appear from the examples which follow.
  • the cyclic anhydride is mixed with the alcohol and heated at 60° C. for 3 hours.
  • the volatiles are removed by distillation under reduced pressure if necessary.
  • the final product can be purified by distillation under reduced pressure.
  • the ester/acid and the thionyl chloride are mixed at room temperature.
  • the reaction mixture can be heated to reflux to complete the reaction.
  • the volatile species are removed by distillation under reduced pressure to obtain the crude product which is typically used as is without any other form of purification.
  • Toluene and trimethylamine are mixed under an inert atmosphere and cooled to -20°C.
  • Dimethylamine DMA
  • the ester/acid chloride is added slowly so as to keep the temperature below 0°C.
  • the mixture is then stirred at room temperature overnight and then filtered to remove the precipitate.
  • the filtrate is evaporated under vacuum to obtain the crude product.
  • the final product is obtained by distillation under reduced pressure of the reaction crude.
  • the cyclic anhydride is added to the primary amine maintaining the temperature below 40°C. The mixture is then maintained at room temperature for 10-24 hours. The volatile species are evaporated under vacuum. The product can be purified by distillation under reduced pressure.
  • the acid amide and the alcohol are mixed at ambient temperature then the thionyl chloride is added slowly so as to maintain the temperature below 30°C.
  • the hydrochloric acid formed during the reaction can be trapped by a concentrated sodium hydroxide solution.
  • the reaction mixture is stirred at room temperature until the starting materials have been consumed.
  • the reaction can be followed by GC.
  • the volatile species are evaporated under vacuum to obtain the crude product. In some cases the crude is dissolved in methanol and the pH adjusted to around 6-7 before evaporation of the solvent. The final product is then obtained after distillation under reduced pressure.
  • Step 1
  • the synthetic route is as follows:
  • the anhydride is obtained by Procedure F.
  • the anhydride is obtained by Procedure F.
  • MGN 2-methylglutaroinitrile (2-MGN) in majority, ethylsuccinonitrile (ESN) and adiponitrile (DNA) is hydrolyzed so as to obtain a mixture called MGA : Mixture comprising 2-methyl-glutaric acid (86% by mole), Ethyl-succinic acid (11% by mole) and adipic acid (3% by mole) A transformation into anhydride is carried out according to procedure F.
  • MGN 2-methylglutaroinitrile (2-MGN) in majority, ethylsuccinonitrile (ESN) and adiponitrile (DNA) is hydrolyzed so as to obtain a mixture called MGA : Mixture comprising 2-methyl-glutaric acid (86% by mole), Ethyl-succinic acid (11% by mole) and adipic acid (3% by mole) A transformation into anhydride is carried out according to procedure F.
  • MGN 2-methylglutaroinitrile (2-MGN) in majority, ethylsuccinonitrile (ESN) and adiponitrile (DNA) is hydrolyzed so as to obtain a mixture called MGA : Mixture comprising 2-methyl-glutaric acid (86% by mole), Ethyl-succinic acid (11% by mole) and adipic acid (3% by mole) A transformation into anhydride is carried out according to procedure F.
  • the acid amide is obtained according to procedure D.
  • Gross product 765g (yellow liquid), >90% by CG
  • the diethyl amide ester is obtained according to Procedure E except that the acid amide is dissolved in dichloromethane before the reaction.
  • MGN 2-methylglutaroinitrile (2-MGN) in majority, ethylsuccinonitrile (ESN) and adiponitrile (DNA) is hydrolyzed so as to obtain a mixture called MGA : Mixture comprising 2-methyl-glutaric acid (86% by mole), Ethyl-succinic acid (11% by mole) and adipic acid (3% by mole) A transformation into anhydride is carried out according to procedure F.
  • MGN 2-methylglutaroinitrile (2-MGN) in majority, ethylsuccinonitrile (ESN) and adiponitrile (DNA) is hydrolyzed so as to obtain a mixture called MGA : Mixture comprising 2-methyl-glutaric acid (86% by mole), Ethyl-succinic acid (11% by mole) and adipic acid (3% by mole) A transformation into anhydride is carried out according to procedure F.
  • Amide-acid n-butanol Thionyl chloride 500g, 2.335mol, 1Eq 270mL, 2.92mol, 1.25Eq 187mL, 2.57mol, 1.1eq MW: 173.21 MW: 74 MW: 118.97, 99%
  • a transamidification reaction is carried out on a mixture of methyl diesters, comprising dimethyl 2-methylglutarate (85% by weight), ethyl succinate (12% by weight) and adipate (3% by weight).
  • the excess dimethylamine is then removed by distillation up to a temperature of 25+/-5° C. and a vacuum of 200 mb, entraining methanol.
  • the condensed mixture of dimethylamine in solution in methanol is recycled in the following charge.
  • the catalytic sodium methoxide is neutralized by concentrated sulfuric acid or by ion exchange resins (sulfonic resins of the Amberlist or Amberlit type).
  • ion exchange resins sulfonic resins of the Amberlist or Amberlit type.
  • the sodium sulphate or the resin is removed from the medium by filtration and rinsed with fresh methanol.
  • the methanol is then removed by distillation under vacuum (up to 120° C. and 10 mb) entraining the unreacted methyl diesters (representing 1% yield); the mixture of methanol and methyl diesters is recycled in the production of the methyl diesters.
  • the product is then distilled under a maximum temperature in the boiler of 140° C. and a vacuum of 5 mb; 4050 Kg are recovered, representing a yield of 92.3%
  • the distillation residue still contains 280 kg of product (yield of 6.3%); it is recycled in the distillation of the following operation.
  • MGN 2-methylglutaroinitrile (2-MGN) in majority, ethylsuccinonitrile (ESN) and adiponitrile (DNA) is hydrolyzed so as to obtain a mixture called MGA : Mixture comprising 2-methyl-glutaric acid (86% by mole), Ethyl-succinic acid (11% by mole) and adipic acid (3% by mole)
  • a transformation into anhydride is carried out according to procedure F.
  • the amide-acid is mixed with the dichloromethane then cooled to approximately 4°C.
  • the thionyl chloride is slowly charged in about 1.5h while controlling the temperature below 25°C.
  • the reaction mixture is stirred at ambient temperature for 10 h.
  • the volatile species are removed to obtain the crude product.
  • Gross product 687g (dark liquid).
  • MGN 2-methylglutaroinitrile (2-MGN) in majority, ethylsuccinonitrile (ESN) and adiponitrile (DNA) is hydrolyzed so as to obtain a mixture called MGA : Mixture comprising 2-methyl-glutaric acid (86% by mole), Ethyl-succinic acid (11% by mole) and adipic acid (3% by mole)
  • a transformation into anhydride is carried out according to procedure F.
  • formulations of various phytosanitary active ingredients, of the emulsifiable concentrate (EC) type are prepared.
  • Example 2.1.1 is a comparative example in which the product Rhodiasolv® ADMA10, Rhodia (Asia Pacific zone): Alkyldimethylamide solvent is used as solvent.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (2)

  1. Verwendung einer Esteramidverbindung, die ausgewählt ist aus den folgenden Verbindungen und ihren Gemischen, als Lösungsmittel in einer Pflanzenschutzmittelformulierung:
    - MeOOC-AMG-CONMe2
    - MeOOC-AES-CONMe2
    - PeOOC-AMG-CONMe2
    - PeOOC-AES-CONMe2
    - CycloOOC-AMG-CONMe2,
    - CycloOOC-AES-CONMe2
    - EhOOC-AMG-CONMe2
    - EhOOC-AES-CONMe2
    - PeOOC-AMG-CONEt2
    - PeOOC-AES-CONEt2
    - CycloOOC-AMG-CONEt2
    - CycloOOC-AEs-CONEt2
    - BuOOC-AMG-CONEt2
    - BuOOC-AES-CONEt2,
    wobei
    - AMG eine Gruppe MGa der Formel -CH(CH3)-CH2-CH2- oder MGb der Formel -CH2-CH2-CH(CH3)- oder ein Gemisch aus den Gruppen MGa und MGb darstellt
    - AES eine Gruppe ESa der Formel -CH(C2H5)-CH2- oder ESb der Formel
    - CH2-CH(C2H5)- oder ein Gemisch aus ESa und ESb darstellt
    - Pe eine Pentylgruppe darstellt,
    - Cyclo eine Cyclohexylgruppe darstellt
    - Eh eine 2-Ethylhexylgruppe darstellt, und
    - Bu eine Butylgruppe darstellt.
  2. Verwendung nach Anspruch 1, dadurch gekennzeichnet, dass das Esteramid einen Schmelzpunkt von weniger als oder gleich wie 20 °C, vorzugsweise 5 °C, vorzugsweise 0 °C, aufweist.
EP09704290.7A 2008-01-25 2009-01-23 Verwendung von esteramiden als lösungsmittel, esteramide als solche, sowie verfahren zur herstellung von esteramiden Active EP2252144B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP18198337.0A EP3520613A1 (de) 2008-01-25 2009-01-23 Verwendung von esteramiden als lösungsmittel, esteramide als solche, sowie verfahren zur herstellung von esteramiden
EP10190722A EP2347652A1 (de) 2008-01-25 2009-01-23 Esteramiden, deren Herstellung und deren Verwendung

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0800393A FR2926699B1 (fr) 2008-01-25 2008-01-25 Utilisation d'esteramides, nouveaux esteramides et procede de preparation d'esteramides
FR0805133 2008-09-18
PCT/EP2009/050780 WO2009092795A1 (fr) 2008-01-25 2009-01-23 Utilisation d'esteramides, nouveaux esteramides et procédés de préparation d'esteramides

Related Child Applications (3)

Application Number Title Priority Date Filing Date
EP18198337.0A Division EP3520613A1 (de) 2008-01-25 2009-01-23 Verwendung von esteramiden als lösungsmittel, esteramide als solche, sowie verfahren zur herstellung von esteramiden
EP18198337.0A Division-Into EP3520613A1 (de) 2008-01-25 2009-01-23 Verwendung von esteramiden als lösungsmittel, esteramide als solche, sowie verfahren zur herstellung von esteramiden
EP10190722A Division-Into EP2347652A1 (de) 2008-01-25 2009-01-23 Esteramiden, deren Herstellung und deren Verwendung

Publications (2)

Publication Number Publication Date
EP2252144A1 EP2252144A1 (de) 2010-11-24
EP2252144B1 true EP2252144B1 (de) 2023-08-02

Family

ID=40900780

Family Applications (3)

Application Number Title Priority Date Filing Date
EP10190722A Withdrawn EP2347652A1 (de) 2008-01-25 2009-01-23 Esteramiden, deren Herstellung und deren Verwendung
EP09704290.7A Active EP2252144B1 (de) 2008-01-25 2009-01-23 Verwendung von esteramiden als lösungsmittel, esteramide als solche, sowie verfahren zur herstellung von esteramiden
EP18198337.0A Pending EP3520613A1 (de) 2008-01-25 2009-01-23 Verwendung von esteramiden als lösungsmittel, esteramide als solche, sowie verfahren zur herstellung von esteramiden

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP10190722A Withdrawn EP2347652A1 (de) 2008-01-25 2009-01-23 Esteramiden, deren Herstellung und deren Verwendung

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP18198337.0A Pending EP3520613A1 (de) 2008-01-25 2009-01-23 Verwendung von esteramiden als lösungsmittel, esteramide als solche, sowie verfahren zur herstellung von esteramiden

Country Status (12)

Country Link
US (2) US8735324B2 (de)
EP (3) EP2347652A1 (de)
JP (2) JP5606925B2 (de)
CN (1) CN101945575B (de)
AU (1) AU2009207634B2 (de)
BR (1) BRPI0905784A2 (de)
CA (1) CA2712318C (de)
ES (1) ES2960114T3 (de)
HU (1) HUE063816T2 (de)
PL (1) PL2252144T3 (de)
TW (1) TW200936045A (de)
WO (1) WO2009092795A1 (de)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7671099B2 (en) 2007-08-13 2010-03-02 Rhodia Inc. Method for spearation crude oil emulsions
FR2950736B1 (fr) 2009-09-25 2011-12-09 Rhodia Chimie Sa Revetements photovoltaiques organiques de morphologie controlee
FR2957492B1 (fr) 2010-03-18 2013-08-16 Rhodia Operations Nouvelles utilisations de composes de type esteramide
FR2957596B1 (fr) * 2010-03-18 2013-07-12 Rhodia Operations Nouveaux composes de type esteramide, leurs procedes de preparation et leurs utilisations
BR112012029752B1 (pt) 2010-05-25 2020-04-07 Stepan Co Composição formadora de película, método de formar uma película, método para melhorar a resistência a esfrega úmida, resistência de bloco, desenvolvimento de brilho,resistência ao acúmulo de sujeira e características de nivelamento de uma película formada a partir de um látex e tinta, formulação de cuidado com piso, formulação adesivalíquida ou produto de calafetar
PL2575446T3 (pl) 2010-05-27 2016-10-31 Preparaty rolne z acylomorfolinami i polarnymi aprotonowymi współrozpuszczalnikami
FR2961206B1 (fr) 2010-06-09 2012-07-20 Rhodia Operations Procede de preparation de composes esteramides
FR2961205B1 (fr) * 2010-06-09 2012-06-29 Rhodia Operations Procede de preparation de composes esteramides
BR112014002607A2 (pt) * 2011-08-01 2017-02-21 Rhodia Operations uso de solventes em favor do meio ambiente para substituir solventes á base de glicol
ES2748387T3 (es) * 2011-10-13 2020-03-16 Rhodia Operations Composición, procedimiento de obtención de la composición y formulación fitosanitaria que la comprende
BR112014010501A2 (pt) * 2011-11-02 2019-02-12 Shah Deepak composição de grânulos dispersíveis em água de liberação variável
US8877846B2 (en) 2012-04-17 2014-11-04 Xerox Corporation Surface coating and fuser member
WO2013158761A1 (en) * 2012-04-17 2013-10-24 Rhodia Operations Polysaccharide slurries with environmentally friendly activator solvents
US20150184001A1 (en) * 2012-06-26 2015-07-02 Solvay Specialty Polymers Italy S.P.A. Fluoropolymer composition
WO2014023593A1 (en) 2012-08-06 2014-02-13 Solvay Specialty Polymers Italy S.P.A. Hybrid fluoropolymer composition
WO2014051442A1 (en) * 2012-09-28 2014-04-03 Nexan Corporation Limited Veterinary pharmaceutical formulations and methods
US20150352502A1 (en) 2012-12-19 2015-12-10 Solvay Sa Method for manufacturing sulfone polymer membrane
WO2014101149A1 (zh) * 2012-12-28 2014-07-03 深圳诺普信农化股份有限公司 农药溶剂及其制备方法和应用
CN103004756B (zh) * 2012-12-28 2015-04-22 深圳诺普信农化股份有限公司 农药溶剂及其制备方法和应用
US9394210B2 (en) 2013-08-23 2016-07-19 Koch Agronomic Services, Llc Urea and nitrogen stabilizer compositions and methods and systems of making and using thereof
EP3055048B1 (de) 2013-10-11 2018-11-07 Solvay Specialty Polymers Italy S.p.A. Verfahren zur herstellung poröser fluorpolymermembrane
JP6783661B2 (ja) 2014-02-28 2020-11-11 ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． 架橋性フルオロポリマー
US20170137658A1 (en) 2014-05-09 2017-05-18 Solvay Specialty Polymers Italy S.P.A. Fluoropolymer compositions
EP3158016B1 (de) 2014-06-19 2018-08-15 Solvay Specialty Polymers Italy S.p.A. Fluorpolymergrundierung mit guter adhesion zu metallen
US20160024320A1 (en) * 2014-07-24 2016-01-28 Kolazi S. Narayanan Mixed solvent based compositions for removal of paint and varnish
BR112017018006A2 (pt) 2015-02-24 2018-04-10 Koch Agronomic Services Llc fertilizante granular de ureia com aditivos de estabilizante de nitrogênio
FR3040995B1 (fr) 2015-09-15 2019-12-27 Arkema France Utilisation de composes comprenant une fonction sulfoxyde ou sulfone et une fonction amide comme solvants et nouveaux solvants
WO2017102405A1 (en) 2015-12-16 2017-06-22 Solvay Specialty Polymers Italy S.P.A. Multilayer assembly
GB201610602D0 (en) * 2016-06-17 2016-08-03 Hercules Inc Micro-porous coating compositions
CN106165692A (zh) * 2016-07-22 2016-11-30 深圳诺普信农化股份有限公司 含有螺虫乙酯的复配杀虫液体制剂
WO2018100324A1 (fr) 2016-12-02 2018-06-07 Rhodia Operations Suspension d'oxyde de cerium
WO2019096800A1 (en) 2017-11-14 2019-05-23 Solvay Specialty Polymers Italy S.P.A. Multilayer assembly
EP3603398A1 (de) * 2018-07-31 2020-02-05 Rhodia Operations Agrochemischzusammensetzung, seine herstellung und anwendung
JP7042353B2 (ja) * 2018-09-10 2022-03-25 富士フイルム株式会社 感光性樹脂組成物、硬化膜、積層体、硬化膜の製造方法、および半導体デバイス
US20230397606A1 (en) * 2020-10-16 2023-12-14 Rhodia Operations Water-soluble concentrate composition
US20220369630A1 (en) 2021-05-06 2022-11-24 Stoller Enterprises, Inc. Stable S-(+)-Abscisic Acid Nonaqueous Liquid Solutions
CN114206828B (zh) * 2021-06-24 2024-01-26 福建省金龙稀土股份有限公司 一种n,n-二烃基酰胺羧酸及其制备方法和应用

Family Cites Families (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE140234C (de) *
DE1040234B (de) 1955-06-07 1958-10-02 Basf Ag Weichmacher fuer Chlorvinylpolymerisate
US3288794A (en) 1962-09-12 1966-11-29 C P Hall Company Of Illinois Method of making amides of dimethylamine and piperazine
US3417114A (en) * 1965-07-20 1968-12-17 C P Hall Company Of Illinois Method of making amides from moisture and acid-gas containing esters
US3809706A (en) * 1971-08-31 1974-05-07 Agriculture N-substituted fatty acid amide lubricants
US4020099A (en) * 1972-10-10 1977-04-26 The C. P. Hall Company Purification of diphenyl terephthalate
DE3339386A1 (de) 1983-10-29 1985-05-30 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung unterschiedlich derivatisierter, in 2-stellung substituierter bernsteinsaeuren
DE3420112A1 (de) 1984-05-30 1985-12-05 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von substituierten bernsteinsaeureamiden
EP0143303A3 (de) * 1983-10-29 1986-04-30 Bayer Ag Verfahren zur Herstellung von substituierten Bernsteinsäureamiden
JP2606324B2 (ja) * 1988-10-14 1997-04-30 住友化学工業株式会社 安定な農薬組成物
JPH02169554A (ja) * 1988-12-22 1990-06-29 Fujisawa Pharmaceut Co Ltd トリメチルアンモニウム塩誘導体およびその製法並びに該誘導体を有効成分とする植物成長調整剤
EP0445096A1 (de) * 1990-02-26 1991-09-04 Monsanto Company Verfahren zur Herstellung von metallfreien Peroxyfettsäurevorläufern mit Amidstücken in der Fettkette
JP3083194B2 (ja) * 1991-02-15 2000-09-04 クミアイ化学工業株式会社 除草剤プロパニルの安定な溶液型組成物及び乳剤型組成物
ZA941843B (en) * 1993-03-18 1995-10-05 Smithkline Beecham Corp Novel Collar to control arthropod infestations of animals
JP3304584B2 (ja) * 1993-12-27 2002-07-22 日本ピー・エム・シー株式会社 ロジン系エマルション組成物、その製造方法、サイズ剤、サイジング方法
PA8515201A1 (es) 2000-04-14 2002-10-24 Agouron Pharma Compuestos y composiciones antipicornavirales; sus usos farmaceuticos y los materiales para su sintesis
DE10301906A1 (de) * 2003-01-17 2004-07-29 Bayer Healthcare Ag Repellentmittel
JP2006522750A (ja) * 2003-04-11 2006-10-05 ノボ　ノルディスク　アクティーゼルスカブ 代謝性症候群ならびに関連の疾患および障害を治療するために、１１β−ヒドロキシステロイドデヒドロゲナーゼ１型阻害剤および抗高血圧剤を使用する併用療法
JP2005015351A (ja) * 2003-06-24 2005-01-20 Nissan Chem Ind Ltd 粒状農薬組成物
US6884906B2 (en) * 2003-07-01 2005-04-26 International Flavors & Fragrances Inc. Menthyl half acid ester derivatives, processes for preparing same, and uses thereof for their cooling/refreshing effect in consumable materials
GB0315684D0 (en) 2003-07-04 2003-08-13 Cooper Howard L A child support arrangement
JP2005306830A (ja) * 2004-04-20 2005-11-04 Tokkyo Joho Service:Kk 害虫駆除剤の撥水性固定散布方法
FR2898356B1 (fr) 2006-03-07 2008-12-05 Rhodia Recherches & Tech Diesters d'acides carboxylique ramifies
FR2902095B1 (fr) 2006-06-09 2008-12-05 Rhodia Recherches & Tech Procede de transformation de composes nitriles en acides carboxyliques et esters correspondants
FR2903983B1 (fr) 2006-07-18 2010-07-30 Rhodia Recherches & Tech Procede de fabrication de diesters.
US20100034766A1 (en) 2006-10-24 2010-02-11 Givaudan Sa Malodor Counteracting Compositions
FR2909088B1 (fr) 2006-11-24 2009-02-13 Rhodia Recherches & Tech Procede de transformation de composes nitriles en acides carboxyliques et esters correspondants
FR2910000B1 (fr) * 2006-12-19 2009-10-16 Rhodia Recherches & Tech Nouveaux composes bis(dialkylamides), procede de preparation et utilisations.

Also Published As

Publication number Publication date
CA2712318A1 (fr) 2009-07-30
TW200936045A (en) 2009-09-01
AU2009207634B2 (en) 2012-12-20
CN101945575A (zh) 2011-01-12
AU2009207634A1 (en) 2009-07-30
JP2014208653A (ja) 2014-11-06
JP2011510046A (ja) 2011-03-31
EP2347652A1 (de) 2011-07-27
US20140221211A1 (en) 2014-08-07
ES2960114T3 (es) 2024-02-29
CN104336010A (zh) 2015-02-11
EP3520613A1 (de) 2019-08-07
WO2009092795A1 (fr) 2009-07-30
HUE063816T2 (hu) 2024-02-28
CN101945575B (zh) 2014-11-19
PL2252144T3 (pl) 2024-04-08
JP5908942B2 (ja) 2016-04-26
US20110166025A1 (en) 2011-07-07
BRPI0905784A2 (pt) 2015-07-14
EP2252144A1 (de) 2010-11-24
US9392785B2 (en) 2016-07-19
JP5606925B2 (ja) 2014-10-15
CA2712318C (fr) 2015-12-08
US8735324B2 (en) 2014-05-27

Similar Documents

Publication Publication Date Title
EP2252144B1 (de) Verwendung von esteramiden als lösungsmittel, esteramide als solche, sowie verfahren zur herstellung von esteramiden
EP2102148B1 (de) Neue bis(dialkylamid)verbindungen, verfahren zu ihrer herstellung und anwendungen davon
EP2280936B1 (de) Verbindungen vom etheramidtyp, herstellungsverfahren und anwendungen
EP2547199B1 (de) Neuartige verwendung von esteramidverbindungen
EP2547651B1 (de) Esteramidverbindungen, verfahren zu ihrer herstellung und verwendung
EP2328862B1 (de) Diamide enthaltendes produkt, verfahren zu dessen herstellung und anwendungen davon
EP2961739A2 (de) Furfuralderivate als eine trägersubstanz
EP2491008B1 (de) Ether-amid-verbindungen und ihre verwendung
FR2926699A1 (fr) Utilisation d'esteramides, nouveaux esteramides et procede de preparation d'esteramides

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20100818

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA RS

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20150929

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

APBK Appeal reference recorded

Free format text: ORIGINAL CODE: EPIDOSNREFNE

APBN Date of receipt of notice of appeal recorded

Free format text: ORIGINAL CODE: EPIDOSNNOA2E

APBR Date of receipt of statement of grounds of appeal recorded

Free format text: ORIGINAL CODE: EPIDOSNNOA3E

APAF Appeal reference modified

Free format text: ORIGINAL CODE: EPIDOSCREFNE

RAP3 Party data changed (applicant data changed or rights of an application transferred)

Owner name: RHODIA OPERATIONS

APBT Appeal procedure closed

Free format text: ORIGINAL CODE: EPIDOSNNOA9E

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

INTG Intention to grant announced

Effective date: 20230223

RIC1 Information provided on ipc code assigned before grant

Ipc: C11D 7/50 20060101ALI20230210BHEP

Ipc: C08K 5/20 20060101ALI20230210BHEP

Ipc: C07C 235/74 20060101ALI20230210BHEP

Ipc: C07C 231/02 20060101ALI20230210BHEP

Ipc: A01N 25/02 20060101AFI20230210BHEP

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE PATENT HAS BEEN GRANTED

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK TR

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

Free format text: NOT ENGLISH

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: DE

Ref legal event code: R096

Ref document number: 602009064942

Country of ref document: DE

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

Free format text: LANGUAGE OF EP DOCUMENT: FRENCH

RAP2 Party data changed (patent owner data changed or rights of a patent transferred)

Owner name: SPECIALTY OPERATIONS FRANCE

P01 Opt-out of the competence of the unified patent court (upc) registered

Effective date: 20230914

REG Reference to a national code

Ref country code: NL

Ref legal event code: FP

REG Reference to a national code

Ref country code: LT

Ref legal event code: MG9D

REG Reference to a national code

Ref country code: AT

Ref legal event code: MK05

Ref document number: 1593548

Country of ref document: AT

Kind code of ref document: T

Effective date: 20230802

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20231103

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20231130

Year of fee payment: 16

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20231202

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230802

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20231204

Ref country code: NO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20231102

Ref country code: LV

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230802

Ref country code: LT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230802

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20231202

Ref country code: HR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230802

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20231103

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230802

Ref country code: AT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230802

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20231215

Year of fee payment: 16

Ref country code: FR

Payment date: 20231212

Year of fee payment: 16

REG Reference to a national code

Ref country code: HU

Ref legal event code: AG4A

Ref document number: E063816

Country of ref document: HU

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20231219

Year of fee payment: 16

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2960114

Country of ref document: ES

Kind code of ref document: T3

Effective date: 20240229

REG Reference to a national code

Ref country code: BE

Ref legal event code: PD

Owner name: SPECIALTY OPERATIONS FRANCE; FR

Free format text: DETAILS ASSIGNMENT: CHANGE OF OWNER(S), ASSIGNMENT; FORMER OWNER NAME: RHODIA OPERATIONS

Effective date: 20240221

REG Reference to a national code

Ref country code: GB

Ref legal event code: 732E

Free format text: REGISTERED BETWEEN 20240222 AND 20240228

REG Reference to a national code

Ref country code: NL

Ref legal event code: PD

Owner name: SPECIALTY OPERATIONS FRANCE; FR

Free format text: DETAILS ASSIGNMENT: CHANGE OF OWNER(S), ASSIGNMENT; FORMER OWNER NAME: RHODIA OPERATIONS

Effective date: 20240318

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20240202

Year of fee payment: 16

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230802

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230802

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230802

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230802

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20230802

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: HU

Payment date: 20231213

Year of fee payment: 16

Ref country code: DE

Payment date: 20231128

Year of fee payment: 16

Ref country code: CH

Payment date: 20240201

Year of fee payment: 16

REG Reference to a national code

Ref country code: DE

Ref legal event code: R081

Ref document number: 602009064942

Country of ref document: DE

Owner name: SPECIALTY OPERATIONS FRANCE, FR

Free format text: FORMER OWNER: RHODIA OPERATIONS, LYON, FR

REG Reference to a national code

Ref country code: DE

Ref legal event code: R097

Ref document number: 602009064942

Country of ref document: DE

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IT

Payment date: 20231212

Year of fee payment: 16

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT